Winter Park FL Property Search

Winter Park FL Homes for Sale

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Winter Park and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

Map & Directions

Available Now in Winter Park - Call Us About These Properties!

$585,000
2 Beds 2 Baths Village Winterset Inc SubDv. 32789 Zip Code
Welcome to the luxury of Winter Park condo living, just steps from the world famous Park Avenue! You will be delighted to step into elegance in this charming first-floor condo with 9' ceilings in the highly sought-after Villages of Winterset Condominiums. Picture this – a simple stroll from your doorstep leads you to Park Avenue's enticing shopping and dining delights, the Morse Museum's cultural treasures, the vibrant energy of Rollins College, the refreshing greenery of the Winter Park Golf course, and the convenience of Sun Rail's commuter train. Immerse yourself in the charm of Central Park, where art festivals, concerts, movies, and events unfold right before your eyes. The Winterset mid-rise building offers key-secured access and a convenient call box for welcoming visitors. The lobby extends a warm welcome with a lounge area, perfect for unwinding or greeting your guests. Indulge in the pristine amenities of this well maintained community – a generously sized private pool, sun deck, and a grilling area designed for your leisure. Now, let's talk about this freshly painted gem of a corner unit – bathed in natural light and adorned with stunning travertine floors. The fully remodeled kitchen (2024) features granite countertops, new cabinets, all new stainless steel appliances and overlooks the spacious dining space. The open-concept dining into living room leads you to the open-entry sunroom that features energy-efficient impact-resistant sliding glass doors that overlooks a paved patio and lush greenery. Both of the bedrooms feature brand new carpet and beautiful plantation shutters that offer privacy and energy efficiency. The welcoming primary suite, boasts a walk-in closet and elegant make-up vanity with a large walk-in tile shower, big enough for two! The guest bath exudes charm with warm wood cabinetry and a tub/shower combo. Live the carefree lifestyle you've been dreaming of in this exclusive Winter Park haven, surrounded by multi-million dollar condos and homes. A property like this will not be available long. Call for your private showing today!

213 E Canton Avenue Unit 213, Winter Park

$115,000
1 Beds 1 Baths Winter Park Woods6-70 SubDv. 32792 Zip Code
Welcome to your new home at 333 Scottsdale Square #333, Winter Park, FL 32792! This fresh listing is perfect for those seeking a blend of convenience and comfort in a vibrant community. This one-bedroom, one-bathroom condo spans 785 square feet, offering a cozy yet functional living space. Ideal for anyone looking to invest, this property provides easy access to everything you need. Situated in the heart of Winter Park, you are mere moments away from bustling shopping centers, a variety of restaurants, and all the entertainment the city has to offer. The theme parks that make Florida a worldwide destination are just a drive away, making this an exceptional spot for fun-loving individuals or small families. In addition, being close to major roads and the airport adds a layer of ease to your daily commute or travel plans, whether for business or pleasure. This condo isn't just a place to live; it's a gateway to experiencing the best of Florida living. Ideal for singles or couples, this property offers a calm retreat without sacrificing accessibility to urban conveniences. Whether you’re a first-time home buyer, a property investor, or simply scouting for a delightful place to settle, this condo checks all boxes. Don't miss out on this opportunity to own a slice of Winter Park, where every day convenience is married to spectacular living. Make Scottsdale Square your new address today!

333 Ne Scottsdale Square Unit 333, Winter Park

$430,000
3 Beds 2 Baths Country Lane SubDv. 32792 Zip Code
Tenant Occupied. Do not Disturb. Welcome to this fantastic home on beautiful Lake Florence in a great Winter Park location off of Howell Branch Road in Seminole County! This spacious 3-Bedroom, 2-Bathroom house features vaulted ceilings, fireplace in the end, ceiling fans, and wonderful outdoor areas. The Living Room, Dining Room and Great Room make this home feel large. The main living areas, hallways and one bedroom have engineered hardwood flooring, wet areas have tile flooring and there is carpet in the Primary Bedroom and Bedroom 3. There is also a small nook that would be perfect for a craft area or office, and it opens to the side courtyard, which is fully fenced and has a storage shed. The Kitchen has all standard appliances including refrigerator, range and dishwasher. There is also an eat in breakfast nook. The Primary Bedroom is in the back of the home and has a nice walk-in closet. The en-suite bath has a shower only. There are sliding glass doors that open to the huge screened-in patio with views into the lake! You will love to wake up to the gorgeous view! There are two additional Bedrooms and Full Hall Bathroom. Each bedroom has access to the screened in porch. This home has a two car garage with opener and washer/dryer hookups. The screened patio, that runs the rear length of the home provides the amazing view to the lake and is perfect for entertaining or enjoying a cup of morning coffee or evening cocktail. Pictures from prior to tenants move-in.

1468 Auburn Green Loop, Winter Park

$3,892,000
4 Beds 5.5 Baths Virginia Heights SubDv. 32789 Zip Code
Welcome to 1391 Richmond Road. A true work of art and surreal living experience now on the market for the very first time. The most discerning buyer will fall in love with the optimal location, an unusually private lot right in the heart of Winter Park, a short stroll to Park Avenue along the stunning shores of Lake Virginia. This handcrafted Georgian style home, designed to emulate New York City townhouse living was masterfully crafted on a magical lot abundant with pristine natural vegetation. Enjoy the Florida lifestyle with frontage on Howell Creek…kayak or paddleboard amongst incredible wildlife to the Winter Park Chain of Lakes. As you arrive, you are greeted by an enticing mix of traditional and old Florida plantings, highlighted by Bevolo exterior lighting and gas lanterns leading the way to your custom mahogany/iron work front entry door. The grand foyer with soaring ceilings, stunning black and white marble flooring, and grand staircase which was built in place, with hand molded railing providing a welcoming signature. Flanked by separate formal living and dining areas on either side, the formal dining room features custom hand painted Gracie brand wallpaper and leads to the butler’s pantry with wine refrigerator. The gourmet kitchen boasts Busby cabinetry, new six burner Decor gas range, new Bosch dishwasher, Subzero refrigerator, large island with prep sink, built-in oven, and naturally lit breakfast area overlooking the backyard oasis. The kitchen opens to the spacious family room with extensive venetian painted millwork, gas/wood burning fireplace with custom Italian made marble surround, 11’4” ceilings, and French doors leading to the terrace and backyard retreat. The formal living room complete with venetian plaster, gas fireplace with custom marble is connected to the family room with a stunning barreled ceiling hallway conveniently located to a chic powder bath. The main floor also includes a full pool bath with access to one of the two garages with air conditioned work room, and a 2nd back staircase. The upstairs primary suite is a sanctuary, graced with an antiqued mirror entry, gas fireplace, double French doors leading to the serene balcony overlooking the statement backyard, and two custom closets with vast cabinetry and lighting. The spa-like bath features Walker Zanger flooring, generous walk-in shower, soaking tub and dual vanities with make-up area. Two additional ensuite bedrooms are also upstairs along with an office/flex room, full bath and laundry room. The second detached garage features a bonus room/convenient home gym. No expense was spared when building which displays antique and unique lighting fixtures, custom millwork, surround sound, central vacuum, reverse osmosis water filtration, and extensive storage throughout. Notable window treatments from the finest textile manufacturers worldwide (Clarence House, Elitis, Nancy Corzine, Carragio), wallcoverings (Fornasetti, Gracie, Schalamandre), lighting (Aerin, Niermann Weeks). This bespoke home is an entertainer’s dream with multiple outdoor areas to relax amongst the secret garden of terraced landscaping and four thoughtfully placed fountains. Celebrate nature’s wildlife which range from owls, great white egrets, blue herons, hawks, bunnies, and otters in your private sanctuary minutes to Winter Park’s premier dining, upscale shopping, Mead Botanical Garden, and the highly coveted Audubon K-8, and Winter Park High!

1391 Richmond Road, Winter Park

$499,000
2 Beds 2.5 Baths Cherokee Park SubDv. 32789 Zip Code
LOCATION, LOCATION, LOCATION! Tucked in a peaceful enclave of Winter Park, this distinctive 2-bedroom, 2.5-bathroom townhome blends mid-century modern charm with contemporary functionality. This home welcomes you inside with an open-concept floor plan featuring a charming wood-burning fireplace flanked by built-in shelving and classic brick flooring that seamlessly connects the living, dining, and kitchen areas, ideal for entertaining and everyday living. The spacious layout flows into the dining and kitchen area with a breakfast bar that invites casual dining, while the kitchen is outfitted with stainless steel appliances and countertops and plenty of cabinetry. The large windows allow for abundant natural light, especially in the upstairs bedrooms, where high ceilings create a sense of openness. Each bedroom offers a plethora of storage with a private ensuite framed by unique clerestory windows, providing privacy while welcoming sunlight and complementing the beautiful wood flooring. Outside, the private backyard offers a generous patio area perfect for hosting epic BBQs or simply relaxing. Experience the best of Winter Park living with this prime location, steps away from the Winter Park Tennis Club and a short stroll to Park Avenue’s acclaimed shops and restaurants, picturesque Rollins College campus, the vibrant Winter Park Farmers' Market, and the scenic shores of Lake Virginia. This home is also a stone’s throw from the exciting up-and-coming Seven Oaks Park, a 1.5-acre green space designed to promote community and wellness through its lush landscaping and thoughtfully curated spaces. Whether you are looking for a standout addition to your investment portfolio or a place to call your own, this property offers endless possibilities. Don’t miss the opportunity to make it yours—schedule a private showing today!

1102 Azalea Lane, Winter Park

$450,000
4 Beds 2 Baths Laurel Spgs SubDv. 32792 Zip Code
**This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome home to this updated 4-bedroom, 2-bathroom home located in the Laurel Springs community of Winter Park! Zoned for top-rated schools, this POOL corner lot home is the next best move for your family. The open concept layout invites you in with the recently updated kitchen at the heart of the home. This space features quartz countertops, stainless steel appliances including a farmhouse sink, floor to ceiling cabinetry, and breakfast bar seating. Make your way around to the family room with the fireplace as the focal point of the room and French doors leading to the outdoor space. The split floorplan features the primary bedroom off the kitchen. This great space features a beautifully updated ensuite with separate vanities and a glass front shower. Off the family room you’ll find the 3 additional great sized bedrooms with the guest bathroom tucked up to the side. Make your way out back to the showstopper of the home! This like new salt chlorinated pool (built 5 years ago) is the perfect space to entertain friends and family year-round with the spacious covered patio extending out to the private pool. Sitting on just under ¼ of an acre this fully fenced lot provides plenty of green space out back and allows space for your RV, boat, or trailer (parking area with 220 power) with no HOA! Recent upgrades include a new pool pump and pool heater with a new compressor. Location is everything with this home being minutes away from Downtown Winter Park, shopping, dining areas, University of Central Florida, and HWY 417. Schedule your private showing today!

3099 Riverbrook Drive, Winter Park

$375,000
3 Beds 2 Baths Eastbrook Sub Unit 05 SubDv. 32792 Zip Code
One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer ~ Charming 3 Bedroom / 2 Bathroom BLOCK HOME on an large CORNER LOT (.23 ACRES) with NEWER WINDOWS and an UPDATED ELECTRICAL PANEL, 2016 ROOF, BAMBOO WOOD FLOORS and MODERN BATHROOMS! The spacious living area flows naturally into the dining area and kitchen with French door access to the patio and FULLY FENCED BACKYARD. The family chef will appreciate a comfortable kitchen offering solid wood cabinetry for ample storage, STAINLESS STEEL APPLIANCES and a window over the sink that lets the light pour in. The bamboo floors continue into the bedrooms including a generous PRIMARY SUITE complete with a RENOVATED EN-SUITE BATH. Bedrooms two and three share a second full bath, also updated! The beautiful mature trees that surround this home create a park-like setting and add privacy for you to enjoy the outdoor space. There is a firepit, garden bed and shed for additional storage. No HOA and zoned for TOP RATED SCHOOLS, the friendly community of Eastbrook is located near SR 436, University Blvd and 417 and is less than 30 minutes to Downtown Orlando. Enjoy the amazing beauty and attractions that Winter Park offers from the Orlando Science Center to the Orlando Museum of Art, Leu Gardens, several lakes, parks, local restaurants, boutiques and so much more! Live, work & play in close proximity to everything you need - call today to schedule a tour!

1880 Viburnum Lane, Winter Park

$675,000
3 Beds 2 Baths Greenview At Winter Pines SubDv. 32792 Zip Code
Situated between tree lined Golfside Drive and the Winter Park Pines Hole 3 fairway, this updated 3-bedroom, 2-bath residence has been completely renovated. Stepping through the front door, you will find an open-concept layout that draws you into the heart of the home. Serving both form and function the engineered hardwood flooring spans the entire home. Built for entertaining, the kitchen is the focal point for all living spaces. The finely finished kitchen has sleek quartz countertops, Whirlpool appliances and a breakfast bar perfect for entertaining or casual dining. The family room is a bright space, complimented by wide double pane windows overlooking the third hole fairway and a wood-burning fireplace. Head outside and be sure to catch the breeze blowing as you relax on the the screened-in patio overlooking the recently planted pine trees along the fairway. Back inside, the Primary bedroom suite has french doors leading outside, a granite topped dual sink vanity and walk in closet. This home has been tastefully updated with notable updates including the entire kitchen, plantation shutters, flooring and neutral paint throughout. The home is zoned for Winter Park schools including Brookshire Elementary, Glenridge Middle and Winter Park High School. You won't want to miss this charming house or the chance to live in this beautiful, established neighborhood. ROOF - 2021.

1336 Golfside Drive, Winter Park

$745,000
5 Beds 4 Baths Enclave At Aloma SubDv. 32792 Zip Code
Welcome to this stunning 3,400+ square foot home, nestled in the prestigious gated community of Enclave At Aloma. Offering a perfect blend of luxury and comfort, this spacious 5-bedroom, 4-full bathroom residence is designed for both entertaining and everyday living. Downstairs, a dedicated home office provides the perfect setting for remote work or quiet study. The generous floor plan allows for a large dining table with seating for 10+ people, with plenty of room to move around comfortably, making it ideal for family and friends. Whether it’s a holiday feast or a casual dinner party, this dining room offers the perfect blend of style and functionality for any occasion. The chef’s kitchen is a culinary dream, featuring stainless steel appliances, granite countertops, a large island, generous storage space, The Kitchen seamlessly flows into the expansive living room designed with an open-concept layout, it provides ample space for relaxation and entertaining. Large windows flood the room with natural light, creating a warm and welcoming atmosphere. The primary suite, located on the second floor, is a private retreat with two large walk-in closet's and an en-suite bathroom complete with a soaking tub, walk-in shower, and dual vanities. Four additional generously sized bedrooms provide plenty of space for family and guests, Step outside to your own private oasis surrounded by beautiful, meticulously maintained landscaping. The screened-in salt water pool offer's a peaceful retreat where you can relax while enjoying the Florida sunshine in complete privacy. The outdoor space also includes a lanai, ideal for unwinding after a long day. Located in a highly sought-after gated community, while being just minutes away from top-rated schools, shopping, dining, and recreational amenities. Don’t miss the opportunity to make this dream home yours!

7945 Pleasant Pine Circle, Winter Park

$5,695,000
5 Beds 5.5 Baths Forest Hills SubDv. 32789 Zip Code
Welcome home to one of the most exceptional properties on the market! This gorgeous, new-construction FG Schaub custom home is the epitome of stunning contemporary design by architect, Michael Weinrich. As you enter this sprawling residence, with views of both Lake Sue and Lake Chelton you'll be greeted by exquisite tile work with brass inlays, wood floors, drop down ceiling, crown molding, wainscoting and natural light that pulls the outside living in. The first floor was meticulously designed with your Owner’s suite, an additional en suite bedroom with walk in closet, large laundry room with full size washer and dryer and an abundance of cabinet and counter space, an eye catching drop zone, elevator, storage room, kitchen and great room. The kitchen truly is a chef’s dream with Quartz countertops, spacious island, custom cabinetry with a satin brass inlay, and modern appliances including Tru refrigerator, freezer, a dual zone 150 bottle wine fridge, 60" Wolfe range with a custom range hood. The custom cabinetry continues into hidden butlers pantry complete with ice maker, microwave drawer, additional sink and Bosch dishwasher. The great room will be your hot spot for entertaining! Located off the kitchen, offering plenty of space for friends and family to gather with easy access to the pool area. Floor to ceiling Anderson windows, bar and an electric fireplace for that added touch of ambiance. Continuing into the Owner's suite you will find more expansive Anderson windows, private access to the outdoor living area, luxurious en-suite bathroom and custom closet. Feast your eyes on the 3x10 large format porcelain tile flooring, dual undermount glass sinks, 24K plated brushed gold fixtures, towel warmer, free standing soaking tub, large walk in shower and private water closet with smart toilet in your Owner’s bathroom. And the closet is a feature in itself with lighted LED rods, custom built ins, full length door mirrors and island. Access the second floor via the private elevator or staircase with a glass railing that leads to 3 additional bedrooms, all en-suite with custom tile work and walk in closets with built ins. You'll also find an additional laundry room with a stackable washer and dryer, linen closet, mechanical room and the activity space complete with wet bar and wrap around balcony with a custom glass railing offering sunsets over Lake Sue. Step outside to your own private oasis featuring a sparkling pool with 3 built in stools, sunshelf and spa, fire pit, and cabana with a full summer kitchen, roll away screens, half bathroom and an outdoor shower - ideal for weekend gatherings or relaxing evening meals poolside. Attention to detail carries out to the oversized 3-car garage which features epoxy flooring and a custom LED light design on the ceiling. While a hand crafted iron gate to the front courtyard gives a nod to Winter Parks favorite resident peacocks. A standing seam metal roof and lush landscaping adds the final aesthetic touch on this FG Schaub masterpiece.

210 Chelton Circle, Winter Park

$409,999
2 Beds 1 Baths Golfview SubDv. 32789 Zip Code
Welcome to this charming beautiful well maintained single family home located in Winter Park, FL. This home has it all! This property features a breezeway entrance / Mudroom that leads you to the front door of the home or to the door to enter the backyard. Presenting 2 bedrooms, 1 bathroom, 1 car garage shared with laundry room space, moving along to the living-room & open eat in kitchen combo. Your large backyard is fenced in to give you privacy while entertaining. It also boasts a covered patio that allows you to enjoy watching the rainfall or sip some lemonade during the sunshiny days. The owner has recently painted the entire exterior and revamped the curb appeal. This home is perfectly situated near downtown Orlando and just minutes from Dubsdread Golf Course and amazing local restaurants. Less than 30 minutes away from your funnest attractions such as Disney, Universal Studios and some great colleges !! Property is currently tenant occupied. Rest assured it’s very easy to show. Here’s your opportunity to own property in Winter Park so schedule your showing today because this won’t last! HVAC: Replaced in 2014 and outdoor unit is rebuilt in 2023 (new compressor) PLUMBING Completely re plumbed in 2009 ROOF- Replaced in 2019 ELECTRICAL replaced in 2009/ Main panel upgraded in 2017 Back Porch built in 2019/ Front Windows replaced in 2018 Exterior Completely repainted: Sept. 2024

1225 Formosa Avenue, Winter Park

Start Your Search